Strong Sad Smiling
From Homestar Runner Wiki
As his name implies, Strong Sad is rarely happy. However, from time to time he manages to crack a smile.
- The Secrets That I Keep — Smiles in a video clip showing a young Strong Bad giving him a noogie.
- Email labor day — When he makes the joke about Strong Bad's invitation being DELETED, he cracks the tiniest of smiles.
- Email extra plug — Watches a picture of Andy Griffith's head taped to the TV with Strong Mad and The Cheat in the basement.
- Email radio — Under the influence of The Deathly Pallor.
- Bug In Mouth Disease — Smiles a bit after Strong Bad suggests he try "putting stuff in quotes" in his search for The Blue Ones.
- Email record book — He gives a big grin for his picture in Strong Bad's book.
- A Folky Tale — Strong Sad grins slightly after he fools Coach Z into thinking he was dead.
- Happy Hallow-day — He smiles involuntarily because of excess sunlight.
- Email looking old — Smiles widely when while talking to a "lace-lifted" Strong Bad, whom he refers to and treats as his great grandmother.
- DNA Evidence — He laughs maniacally about how the world will never know the truth about the DNA evidence.
- Ever and More! — Smiles after he begins believing in the message.
- Email concert — Smiles when mocking Strong Bad's outfit, and after entering the room when Strong Bad is telling Homestar Runner about sloshy.
- Email pizza joint — Smiles as he reviews The Pizz in Review Revue.
- Email nightlife — He smiles after explaining to Marzipan how he spends his time at Club Technochocolate not dancing.
- Somber Vacation — Strong Sad smiles in a picture of him holding his favorite tropical beverage and also in a postcard from Depressio Beach.
- Most in the Graveyard — Strong Sad smiles when he wonders if he has "willed [himself] to death".
- Coach Z's 110% — Strong Sad smiles as the narrator speaks.
- Kick-A-Ball — Strong Sad smiles when he gets picked.
- 79 Seconds Left — Strong Sad smiles when he pours water on his knee.
- Email hremail 3184 — Strong Sad smiles while eating his pop-tart (with a vengeance).
- Email imaginary — Lil' Strong Sad smiles while playing with Scotty Titi.
- Compy Catalog — Strong Sad smiles while singing his song about the mail arriving.
- Email independent — Strong Sad smiles when talking about his film school degree, and also after mentioning Art's House.
- Doomy Tales of the Macabre — Strong Sad smiles after all the characters come for a surprise party.
 Screenshots of Strong Sad Smiling
Ah, the (dumpy) memories..
"Oh, hello, pleatèd boots."